Ethanol → Ethyl 2-bromo-2-(4-chlorophenyl)acetate

HRID 1583965Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Br:16]Br.[CH2:18](O)[CH3:19]>>[Br:16][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH2:18][CH3:19])=[O:10]

Participants

Reactant 4

HCID 702Ethanol

HCID 15880(4-Chlorophenyl)acetic acid

HCID 24386Thionyl Chloride

HCID 24408Bromine

Product 1

HCID 228840Ethyl 2-bromo-2-(4-chlorophenyl)acetate

Procedure

By the method of E. Schwenk and D. Papa, J. A. C. S. 70, 3626 (1948), incorporated herein by reference, 86.8 g (0.509 mole) of p-chlorophenylacetic acid was treated with 100 ml of thionyl chloride. Subsequent reaction with 83.2 g (0.52 mole) of bromine followed by 100 ml of ethanol produced 78.9 g of ethyl alphabromo-(4-chlorophenyl)acetate as an oil.

Sources & evidence

ORD record: ord-4caa30742950480880aa154bff8131dd
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04555521

Reaction notes

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